Just Another Hustler in the Hustler Kingdom

A little more than a month ago, after former Rep. Bob Barr started to edge into the Libertarian Party’s presidential race, I had an idea. Former Sen. Mike Gravel, a former Democrat, was already gunning for the nomination. It wasn’t every year that politicians of the Left and the Right ditched the parties they’d spent their entire careers in to become Libertarians. I started planning an event with both candidates, jokingly promoting it on Facebook as a “great debate.”

I got a call from Wayne Allyn Root.

“What’s this I’m hearing about a Libertarian debate?” Root said. “How are you going to have a Libertarian debate without the guy who’s going to be the nominee?”

He laughed, but he was serious about this. When I wrote an early prognosis on the Libertarian race, I said Root — a sports prognosticator and gambling guru who’s hosted TV shows, radio shows, and motivational speaking junkets — was running third behind Barr and movement speaker and author Mary Ruwart. Root had called to point out that he, not anyone else making a run at the nomination, was on the phone with delegates every spare minute he had. Every minute, at least, that he wasn’t spending with me. “I’m calling up every one of these people who will actually be voting for the nominee!” Root said. “I talk to 25 or 30 of them every day!”

Root did talk to those delegates, missing only a handful, leaving messages on their machines. And he charmed his way into the forum I set up with Barr and Gravel. I watched as reporters flipped out cameras and digital recorders to capture the wisdom of the former senator and the lion of the Clinton impeachment, then saw Root struggling to convince them that he, too was a frontrunner. The day after the forum, Root called to laugh about the Washington Post‘s photo of the event, which cropped him out. “I’m going to frame that and put it on my wall.” He laughed again.

In Denver, as the LP settled on its ticket, Root got his bragging rights. On the party’s fifth ballot, he fell short of the party’s nomination but held a stockpile of delegate votes that made more than the difference between Barr and Ruwart. He took the stage, pumping his fists. “I want to spend the next year learning from the master,” Root said. “Barr/Root ’08! Come on, let’s bring it home!” The guy the national media mostly ignored ended up on the highest-polling (at this moment, at least) Libertarian ticket since the Reagan years.

WAYNE ALLYN ROOT is a failure. He’ll tell you as much. He’s “the world’s most successful failure,” a man who stumbled from job to job, succeeding at none of them, before he found the one that made him a millionaire. He used to be a Republican, then decided to become the Libertarian Party’s presidential nominee. When he fell short, he threw his votes to Bob Barr and became the ex-congressman’s running mate. What Wayne Root wants, Wayne Root gets. Sort of.

The little attention that the LP’s ticket has received has centered, mostly, on Barr. The evolution of a Republican drug warrior into a Libertarian war horse is an odd, twisty story. Root’s story is almost as entertaining. He is, in his own words, “the world’s most successful failure.” His first general-interest book (he’s written six of them, most about the art of gambling) was titled The Joy of Failure, and it revealed how he’d basically talked his way into a glamorous career with a bullish sales plan papering over his lack of qualifications.

As Root tells it, he tried, and failed, at thirteen different careers. He was rejected from law school. He failed as a realtor four different times, blowing tens of thousands of dollars on brochures for properties no one bought. He managed a Manhattan restaurant, then “got bored and quit.” He became an entertainment agent, signing one client, and snagging him one job — in six months. His biggest innovation was “Ivy League Home Cleaners,” a maid service staffed with college graduates, none of whom, quite understandably, wanted to become maids.

Root’s breakthrough came when he realized what he really wanted: to be a sports prognosticator. He decided to become “greatest sports prognosticator in the world,” officially, sending out hundreds of press releases with that tagline, assuring reporters that they had to know about Wayne Allyn Root. Thanks to a few newspapers with feature holes to fill, the P.R. offensive paid off. Root founded a company (which failed) and wrote a book on risk (also a failure), but every little piece of credibility got him closer to TV personality status. Once he made it on TV, he was in: No one could take his fame away from him. His formula for success, he discovered, was something he could bottle and give to everybody. He taught it to his wife when she put on 80 pounds during her pregnancy. “She started living my program. The pounds started to melt off!”

WITH ALL OF THAT behind him, how could Wayne Root not get into politics, the domain of district attorneys and trial lawyers and promotion-seeking chiefs of staff? “My entire life has been a PERFECT preparation for politics,” Root told the Gambling Newswire in 2005. “I’ve spent the last 20 years giving interviews with the media. I’m on national TV more than any politician in the state of Nevada!” (This was before the still-mystifying triumph of Sen. Harry Reid.) In 2005, Root published a sort of sequel to his first self-help tome dubbed Millionaire Republican, telling readers that “thinking like a Republican,” taking risks and cutting throats, was the surest path to success.

Some sections of the book didn’t hold up so well. “This professional prognosticator,” Root wrote then, “believes that the GOP will dominate American politics (on all levels) for the foreseeable future.” But by mid-2006, Root was telling Republicans that they were throttling their message and their voters by building up big government, and by cracking down on gamblers. By early 2007, he was exploring his Libertarian Party bid. And by the time he took the stage with Bob Barr, on a national political ticket at last, Root was crowing about making his old party irrelevant, for reasons no other Libertarian had thought of. Like:

“There are 50 million poker players in this country, and 12 million online poker players. For the first time, they have a candidate they can support!”

And:

“I am the first small businessman to run on a national ticket!”

And:

“I’m a home school parent, and education is, to me, the civil rights issue of our time!”

The Pulitzer-winning historian Walter McDougall has diagnosed the United States as a “nation of hustlers.” He means it in a good way; Americans are Horatio Alger heroes, constantly scheming and one-upping and finding new ways to win. If you’re a skeptic, you might think see Root’s success as a confluence of lucky breaks, impossible to repeat for anyone not gifted with superhuman salesmanship or — as my colleague Jesse Walker has put it — “the comportment of a Ronco pitchman with a squirrel in his pants.” If you buy McDougall’s theory, stop rolling your eyes at the guy. Wayne Allyn Root wants you to be able to become the next Wayne Allyn Root. And you should take him up on it.

“I’m an S.O.B.,” Root likes to joke. “A son of butcher. America needs an S.O.B. in the White House!”